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Configuring Postfix to Send Mail from Mac OS X Mountain Lion

I recently upgraded my Mac to use Apple’s latest operating system, Mountain Lion, and in so doing, wiped out my postfix configuration that I had previously set up with advice from many different blogs. Postfix is essential for my line of business where I send many emails through MAMP on my local machine.

After hours of updating settings and getting nowhere, I stumbled across a blog post that set me in the right direction.

Rather than do this process again when Apple releases a new upgrade, I decided to document the steps I took to get this working (more for a reference for myself, but also to help those with the same issues).

I personally use Google Apps, so this process is for those also trying to authenticate through Gmail.  This process is much simpler if you don’t need SSL encryption when sending mail.  I use TextMate as a text editor, so the following command line options use the ‘mate’ command.  Alternatively, you can use ‘vi’, ‘vim’ or ‘nano’ depending on what you are familiar with.

Step 1

First, we need to create a Simple Authentication and Security Layer (SASL) password file.  To do this, open up Terminal and enter in the following command:

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sudo mate /etc/postfix/sasl_passwd

You will be required to enter your root password to edit the file. Enter in the following information, replacing <username@domain.com> with your google apps username and domain or your gmail account, and <password> with your password:

Save and exit.

Step 2

Next, we need to create a postfix lookup for our new SASL password file.  To do this, type the following command in the Terminal:

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sudo postmap /etc/postfix/sasl_passwd

Step 3

Then we need to configure Postfix’s main.cf file which has all the configuration information for Postfix.  I would recommend backing up this file in case anything happens.  The first line of the following commands does just that, by creating a copy before editing it:

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sudo cp /etc/postfix/main.cf /etc/postfix/main.cf.orig
sudo mate /etc/postfix/main.cf

Most of the information here is commented out.  You just need to scroll down to the bottom and paste in the following lines:

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# Minimum Postfix-specific configurations.
mydomain_fallback = localhost
mail_owner = _postfix
setgid_group = _postdrop
relayhost=smtp.gmail.com:587

# Enable SASL authentication in the Postfix SMTP client.
smtp_sasl_auth_enable=yes
smtp_sasl_password_maps=hash:/etc/postfix/sasl_passwd
smtp_sasl_security_options=

# Enable Transport Layer Security (TLS), i.e. SSL.
smtp_use_tls=yes
smtp_tls_security_level=encrypt
tls_random_source=dev:/dev/urandom

Save and exit.

Step 4

At this point, we just need to start up Postfix with our changes.  Use the following command:

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sudo postfix start

If you entered in any information incorrectly in the main.cf file, this may throw errors.  Fix the errors and then reload Postfix:

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sudo postfix reload

Step 5

You can test this configuration by sending a test email from Terminal:

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date | mail -s test youremailaddress@yourdomain.com

If all goes well, you should receive an email to your inbox.

Step 6

Once you have everything working, you can set Postfix to start on boot by adding a key to /System/Library/ LaunchDaemons/org.postfix.master.plist file.

The key to add is:

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<key>RunAtLoad</key>
<true/>

The updated file looks like this (text version below):

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<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple Computer//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
<dict>
  <key>Label</key>
  <string>org.postfix.master</string>
  <key>Program</key>
  <string>/usr/libexec/postfix/master</string>
  <key>ProgramArguments</key>
  <array>
    <string>master</string>
    <string>-e</string>
    <string>60</string>
  </array>
  <key>QueueDirectories</key>
  <array>
    <string>/var/spool/postfix/maildrop</string>
  </array>
  <key>AbandonProcessGroup</key>
  <true/>
  <key>OnDemand</key>
  <true/>
  <key>RunAtLoad</key>
  <true/>
</dict>
</plist>

And that’s it! You should now be able to send mail using Mac OS X and Postfix from a PHP install. I am not an expert at this by any means, but feel free to leave a comment below letting me know if this helped you or if you have any issues with it. I would be glad to help in any way I can!


97 Comments

  • Reply P |

    You, sir, are a genius. I finally got PHP mail() working on my Mac. I cannot thank you enough.

  • Reply songyy |

    Hi thanks for your article. I’ve followed every steps from this tutorial; but it doesn’t work on my Laptop… so I went ahead and followed the blog post you mentioned at the start of the message, but also doesn’t work.

    I also googled this post:
    http://slashusr.wordpress.com/2012/02/14/enabling-postfix-for-outbound-relay-via-gmail-on-os-x-lion-11/
    Still it doesn’t work. I’m having this error message when I enter “mail” command to check new mail:

    : host smtp.gmail.com[209.85.225.108] said: 530-5.5.1
    Authentication Required. Learn more at 530 5.5.1
    http://support.google.com/mail/bin/answer.py?answer=14257
    aa4sm11414435igc.15 (in reply to MAIL FROM command)

    Do you have any idea with it?

    • Reply Benjamin Rojas |

      songyy,

      I am not sure what the issue is. As long as you are following all the steps correctly, it should work for you. Gmail is a secure mail server and requires authentication, but the above steps should do the trick. Have you confirmed that your credentials are correct?

    • Reply Mark |

      I know this is a late reply, but for any additional searchers:
      1. I don’t know if you need to do this, but it seemed to make a difference after you change the password file rerun: sudo postmap /etc/postfix/sasl_passwd
      2. If you have enabled 2-step authentication make sure you generate a application password to use instead of your normal password

      Anyway those were just thigns that *seemed to get mine running.

      • Reply Chris Weekly |

        @Benjamin, kudos for a great guide.

        @Mark, high five for clarifying the need to generate and use an app-specific password for those of us (everyone, nowadays, right?) using 2-factor auth.

        THANKS, BOTH OF YOU!

  • Reply Rob Gregg |

    Wow, best guide for configuring postfix on OS X yet I’ve read. So straight forward and easy to read, and everything worked as expected the first time.

    Great job!

  • Reply Daza Grohovaz |

    Hello,

    i use Mountain Lion with the Server Application.
    looking in the mail.log file, i just realized that MacOSX Server didn’t set all rights like i should do…

    1. look in the log file

    tail -f /var/log/mail.log

    2. if you get this message, you have the same problem that i had

    Oct 3 11:48:54 MacOsX.Server postfix/postfix-script[59779]: warning: not owned by _postfix: /Library/Server/Mail/Data/mta/./guid_device_maps.plist

    3. check the rights and privileges of the file guid_device_maps.plist

    sudo ls -al /Library/Server/Mail/Data/mta/./guid_device_maps.plist
    -rw-r—– 1 root mail 181 Sep 18 07:40 /Library/Server/Mail/Data/mta/./guid_device_maps.plist

    4. change the owner to _postfix user

    sudo chown _postfix /Library/Server/Mail/Data/mta/./guid_device_maps.plist

    5. check your changes 😉

    sudo ls -al /Library/Server/Mail/Data/mta/./guid_device_maps.plist
    -rw-r—– 1 _postfix mail 181 Sep 18 07:40 /Library/Server/Mail/Data/mta/./guid_device_maps.plist

    6. open the Server Application, go to Email, check the Authentication method, i set it as “Automatic”

    7. finally restart it switching on/off

    sorry if the description isn’t 100% correct, i have my system in german, but i think you know what i mean…

    regards

  • Reply samiam |

    Hi ben

    I’ve tried your config tutorial and I’ve been unsuccessful.
    I wanted to run it by you to see if I’m just missing a simple step.

    I’m using MAMP
    1. I changed the settings in the php.ini file to

    [mail function]
    ; For Win32 only.
    SMTP = localhost
    smtp_port = 25

    ; For Win32 only.
    ;sendmail_from = me@example.com

    ; For Unix only. You may supply arguments as well (default: “sendmail -t -i”).
    ;sendmail_path =/usr/sbin/sendmail -t -i -f myusername@gmail.com

    2. I created the sasl_passwd in the postfix directory adding this text

    smtp.gmail.com:587 :

    3. added the text you recommended to the master.cf file

    4. I tried to run this code from terminal and looked in gmail but nothing posted in the inbox or in the spam folder.

    date | mail -s test myusername@gmail.com

    5. I also tried to run a test php mail() through MAMP and received this apache error code

    [Mon Jan 07 00:11:29 2013] [notice] Digest: generating secret for digest authentication …
    [Mon Jan 07 00:11:29 2013] [notice] Digest: done
    [Mon Jan 07 00:11:29 2013] [notice] Apache/2.2.22 (Unix) mod_ssl/2.2.22 OpenSSL/0.9.8r DAV/2 PHP/5.4.4 configured — resuming normal operations
    [Mon Jan 07 00:11:39 2013] [error] [client 127.0.0.1] client denied by server configuration: /Applications/MAMP/htdocs/.DS_Store

    I’m not really sure where I’ve gone wrong on this, I imagine its something basic, but I’m not sure if it’s a setting in gmail or I’m just missing a step.

    any help would be appreciated.

    best,
    SAM

    • Reply Benjamin Rojas |

      Sam,

      For the recored, I am also using MAMP, but didn’t change anything within the MAMP configuration (php.ini or anywhere).

      On your step 2, did you put in your Gmail email and password? Or did you just have a blank : ?

      When sending mail from terminal, try sending it to a different email address then the one you are sending from, just to make sure that everything is working right.

  • Reply George |

    hello guys. i have used this example and it worked fine until the step 5. when i used a simple example in my code
    $txt = “First line of text\nSecond line of text”;
    $txt = wordwrap($txt,70);
    mail($toemail,”My subject”,$txt);
    is still not working. im having this error message “Error 324 (net::ERR_EMPTY_RESPONSE): The server closed the connection without sending any data.” how i can fix it? thank you

    • Reply Benjamin Rojas |

      George,

      This sounds like an external problem, not related to the Postfix issue. Are you still getting this error? Were you able to figure it out?

  • Reply super |

    any idea why i am getting this?

    Macs-MacBook-Pro:postfix Mac$ sudo postmap smtp_sasl_passwords
    postmap: warning: smtp_sasl_passwords, line 1: expected format: key whitespace value
    postmap: warning: smtp_sasl_passwords, line 3: expected format: key whitespace value
    postmap: warning: smtp_sasl_passwords, line 4: expected format: key whitespace value
    postmap: warning: smtp_sasl_passwords, line 5: expected format:

    my smtp_sasl_passwords file has:
    smtp.gmail.com:587 myrealemail@gmail.com:mypass

    • Reply Benjamin Rojas |

      super,

      I am not sure why you are getting these messages, but if you copied and pasted anything, I would try removing all text from the file, and typing it in by hand. That way if there are hidden characters that are causing these errors, they will be removed.

  • Reply Steve Adams |

    Thanks for your help in configuring Postfix, gave me the pointers I needed to get my mail command working with our security policies at work

  • Reply matteo |

    Thank You So much!!!
    Just a last question, the file /etc/postfix/sasl_passwd what kind of permission should have? It is safe to keep the password in that file whithout changing permission and/or owner?
    Thank you again!

    • Reply Benjamin Rojas |

      matteo,

      My current sasl_password file is set pretty secure. It is a system file so I have it set to system permissions. My local username does not have access to it and I can only edit it with administrative access.

  • Reply Jason |

    Does this allow you to send email within MAMP via SMTP as well? For instance, when using MAMP and the Swift Mailer library with the SMTP transport.

    I’ve been trying and so far have no luck:
    host: smtp.gmail.com
    port: 587 // also tried 25 & 465
    encryption: tls
    username:
    password:

    • Reply Benjamin Rojas |

      Jason,

      This method does incorporate SMTP directly through the google account. This is how I am sending out the messages in the first place, as you can see through step 1. My SMTP address is set with my username and password for authentication.

  • Reply WordWeaver |

    Thank you very, very much Benjamin for your clear, precise instructions.

    I followed your instructions to the letter, and only encountered one problem at the very end when I attempted to start up postfix.

    The problem was that there was no “spool” directory. However, a quick Google search showed me exactly what I had to do in order to create it.

    Once I created the “spool” directory, postfix began working just great.

    Once again, thank you so very much sir for saving me hours of needless hassle and headaches. :)

  • Reply ttmt |

    I’ve been trying to do this for days and I keep getting the same error in terminal after step 4.

    postfix: fatal: chdir(/Library/Server/Mail/Data/spool): No such file or directory

    Can anyone help with this.

  • Reply James Clavel |

    I just implement the methods specified above and worked like magic. although I have been using a different tutorial before on my Snow Leopard, now I just got a new mac mini and set it up for my web development workhorse. Now can use local development as for Email function testing. thanks and definitely worth a space on my bookmark!

  • Reply theodoros |

    Dear Ben,
    thank you for your post. I found something relevant at http://blog.deversus.com/2012/07/fix-for-postfix-in-mac-os-x-10-8-mountain-lion/#comment-18035 , by MIKE WALSH on JULY 26, 2012
    where in combination with your post, i finally solved my problem
    I followed your post but i stuck, at step 5.
    Then at by MIKE WALSH’s post at the end i noticed the source of my problem (error: sendmail: fatal: chdir /Library/Server/Mail/Data/spool: No such file or directory). Then I followed the instructions there and I created the directory /Library/Server/Mail/Data/spool
    and then the problem for me was solved !!
    Anyway.., Thank you (both you and MIKE) so much
    Theodoros

    • Reply Joe J. |

      Can some please explain then how all emails to my system are being routed to /var/mail/ file? (Thus, when routed there, the user’s Mail never receives them since it’s not with the regular MAILDIR directory – and no, moving them there, or link to it does not work -> I tried)

      This has me befuddled and wanting to shoot the computer. I have NOT set:

      # DELIVERY TO MAILBOX
      #
      # The home_mailbox parameter specifies the optional pathname of a
      # mailbox file relative to a user’s home directory. The default
      # mailbox file is /var/spool/mail/user or /var/mail/user. Specify
      # “Maildir/” for qmail-style delivery (the / is required).
      #
      #home_mailbox = Mailbox
      #home_mailbox = Maildir/

      If I turn on the “Maildir/” option -> then mail is routed to /Users//Maildir

      I cannot for the life of me get it to route to where the IMAP daemon is reading it’s files. I can verify that when I send from one user to another on my system (from outside the domain) – the .SENT MESSAGES folder DOES show the email being sent – so it does find those in the MAILDIR structure – it’s only when sending out that it doesn’t work.

      Is there some parameter, setting, blessing to some mail goddess that will get this to correctly route out?

      I really need some help here.

      If you need to see my main.cf -> please let me know and I’ll forward it – but I can assure you, I’ve bareboned it as much as I can to no avail.

      thanks.

      Joe…

      • Reply Joe J. |

        Fixed. For those who want to know how – look at this configuration in

        main.cf
        (that file is in: /Library/Server/Mail/Config/postfix)

        The item is:

        mailbox_transport = dovecot

        Seems in the migration from whatever to 10.8, that item is commented out and not set to a default setting. Unfortunately, postfix on Server uses dovecot to actually deliver the messages to the Maildir directories. So, since this wasn’t set, postfix had no way to figure out how to get it to the correct user (who’s directory is really their GUID)…

        Here’s a quick test: enable to two accounts on your box. Then from out side, have account Bob send to account Alice.

        Now, go to Bob’s Maildir -> this will be located in:

        /Library/Server/Mail/Data/mail/

        (you need to determine his GUID – I did it the hard way by looking at the messages in the accounts until I found the ones that matched my user name – there’s another way people said to do it, but it never worked for me)

        Anyway, back to our regularly scheduled explanation: now, look in Bob’s Maildir under his .Sent Messages directory. In there you should see a corresponding message saying he sent the message.

        Go back to Alice’s Maildir and look under the “cur” or “new” directory. If the message from Bob isn’t there – then dovecot is not routing correctly.

        To find out where it’s routing – there are 3 possibilities:

        1) it’s under /var/mail/ (note: not GUID – their account name) – and it’s all in one file – this uses the old style pre-Maildir format for storing the Inbox messages.

        2) It’s under /Users//Maildir – in this case, postfix has given it to dovecot, but dovecot can’t figure out how to handle it – or, you’ve enabled home_mailbox = Maildir/ in main.cf.
        (this is bad. For ML you don’t need to set this, the server admin does this automatically – and when you turn this on this way, the routing ends up in that setup.

        3) It’s somewhere else on your machine – and this one is probably related to the imap:default_partition setting – go check that out by looking at:

        serveradmin settings mail:imap

        Anyway, any of those three are bad – all you really need to do is set the setting above to get the transport agent working correctly.

        Just as an aside, the way I kinda think of things (someone will probably slam me for this analogy, but hey, it’s my head and it works) – postfix is the USPS – it handles getting mail and putting them to the correct post office. Getting it to your door (your inbox) is handled by dovecot. IMAP is nothing more than reading those directories for new items.

        Hope this helps someone else – especially since it took me almost three days of constant researching to finally find out what was wrong with my mail.

        I can post my main.cf if anyone cares -just shoot me an email.

        Joe…

  • Reply Gerardo |

    Hi, just a simple and maybe dumb cuestion. Do I need MAMP to make this work?

    • Reply Benjamin Rojas |

      No, You do not need MAMP. This is just the configuration I used in conjunction with MAMP.

  • Reply Andrey |

    I also recommend to execute that command after creating password file:

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    sudo chmod go-rx /etc/postfix/sasl_passwd

    The chmod go-rx sasl_passwd removes the group and other/world read/execute permissions on the password files. Only the root user should be able to read it.

  • Reply Alan |

    Can anyone help me clear up the Mountain Lion Server requirements and conflicts?

    Sorry for my apparent ignorance and confusion. I want to clean things up and make mail work again.

    On Lion Server all was well. Since upgrade to ML Server I cannot get mail (“mail -s …..” from command ine) to send.

    ON ML Server there are 2 separate paths to very similar files:

    a. /etc/postfix
    b. /Library/Server/Mail/postfix

    On an ML Server:

    1. Which path is being read?
    2. How can I tell?
    3. Can I safely ignore or remove one of these paths?
    4. How can I choose the path least likely to be mucked up by the next OS update?

    Thank you for your help.

    -alan

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  • Reply Ralph Pass |

    To get postfix to start on boot on my Mountain Lion computers I needed to change the OnDemand from true to false. After that, it starts on boot, every time

  • Reply Eric |

    Thanks for the awesome post, tried many other ways to get mail working with MAMP and this post was the only one that actually worked.

  • Reply John |

    You could simplify this by guide by replacing steps 1 and 2 with writing this into the main.cf:

    smtp_sasl_password_maps = static::

    It sidesteps the need for a user/passwd file by embedding it directly into the main.cf.

    • Reply Benjamin Rojas |

      Bercana,

      Sorry for the late reply. Did you ever get this working? Sounds like this is an issue with sudo not working properly. Did you use the correct password to get sudo access?

  • Reply John Dial |

    Upgrading to Mavericks prevents postfix from working for some reason. Of course this happens right before a very important demo. I spent serveral days trying to restore email, until I found this article.

    Thank you very much for taking the time to share your knowledge and experience. You have no idea how much it can mean to the person on the other side of those words.

  • Reply Steve Sawin |

    This is great, but when I do all that mail does not return an error message, but fails to send. The file /var/log/mail.log just has many copies of the message postfix/tlsmgr[11408]: exiting to reopen external entropy source dev/urandom

    Suggests some problem with the dev/urandom thing, but I cannot tell what. Any suggestions?

  • Reply Fabrizio |

    It doesn’t work.
    When I send mail I see it in queue (using mailq command)
    in mail.log i got this:

    connection refused
    TLS is required, but our TLS engine is unavailable
    connect to smtp.gmail.com:587: No route to host

    I have a Mac Book with Mac OS X 10.9.1
    It’s pretty new and I have never touched any other config file

    Any suggestions?

    • Reply Fabrizio |

      Fixed! The problem was connected to a previous configuration of MAMP PRO.
      It was infact creating a custom main.cf file which had some wrong parameter.
      I have just restored the original file and followed the instructions above and bang! that’s it!
      Thanks for the tip!

  • Reply Nkongme |

    Not too many howtos out there, where every step functions. Well done. Respect!

  • Reply Mike iLL |

    Thanks for the well written, informative article, man. Helped get me through struggle after having upgraded to mountain lion, then back to snow leopard, but at some point smtp had stopped working. I hope you can remove the bullet sales-people from the above commentary. : )

  • Reply matt |

    I had this issue at step 2 :

    postfix: fatal: parameter inet_interfaces: no local interface found for 0.0.0.0

    In main.cfg comment out the following line :
    inet_interfaces = localhost
    ( or inet_interfaces = all )

  • Reply Sam Ciaramilaro |

    Brilliant! Thanks a bunch.

    And thanks to @Mark for the tip on rerunning -> “sudo postmap /etc/postfix/sasl_passwd” after saving the password file.

  • Reply John Wooten, Ph.D. |

    I have followed your instructions and this is working perfectly on my MacBookPro running Mavericks 10.9.2. I have a server, which is a MacMini which is running Mavericks Server 10.9.2. I copied the files from my MacBookPro to the server, put them in the proper places /etc/postfix, checked their permissions, did the postmap, then reload. Sent a trial email, but I never arrives to my account. Is there a log where I could find if there is an error? Both my laptop and server on on the same local network with both having access to the outside world.

  • Reply John Wooten, Ph.D. |

    I am seeing in the log:
    Apr 19 13:05:25 jwooten37830.com postfix/cleanup[35785]: 227A83C18257: message-id=
    Apr 19 13:05:25 jwooten37830.com postfix/qmgr[32382]: 227A83C18257: from=, size=294, nrcpt=1 (queue active)
    Apr 19 13:05:25 jwooten37830.com postfix/smtp[35787]: connect to smtp.gmail.com[2607:f8b0:400d:c00::6c]:587: No route to host
    Apr 19 13:05:26 jwooten37830.com postfix/smtp[35787]: 227A83C18257: to=, relay=smtp.gmail.com[173.194.68.108]:587, delay=1.7, delays=0/0/0.71/0.99, dsn=2.0.0, status=sent (250 2.0.0 OK 1397927134 j7sm62555545qab.27 – gsmtp)
    Apr 19 13:05:26 jwooten37830.com postfix/qmgr[32382]: 227A83C18257: removed

    No route to host?

  • Reply Raz |

    This worked brilliantly ! Thanks

    I worried when I was using 2 factor auth on Hotmail, however you can generate one time password.

    Some of the information in Step 3 already exists in the config file

    Thanks again 😀

  • Reply Thomas Gagne |

    Did the Yosemite upgrade break anyone else’s configuration? I’ve not changed my email or password…

    Since the upgrade I’m getting:
    Oct 22 13:35:38 DrozBook.local postfix/smtp[2466]: BA6451148F62: SASL authentication failed; cannot authenticate to server smtp.gmail.com[74.125.192.108]: generic failure
    Oct 22 13:35:39 DrozBook.local postfix/smtp[2466]: BA6451148F62: to=, relay=smtp.gmail.com[74.125.192.109]:587, delay=6914, delays=6913/0.07/0.96/0, dsn=4.7.0, status=deferred (SASL authentication failed; cannot authenticate to server smtp.gmail.com[74.125.192.109]: generic failure)

    • Reply Thomas Gagne |

      Perhaps it’s the new version of postfix?

      DrozBook:postfix tgagne$ sudo postfix reload
      /usr/sbin/postconf: warning: /etc/postfix/main.cf: unused parameter: use_sacl_cache=yes
      /usr/sbin/postconf: warning: /etc/postfix/main.cf: unused parameter: imap_submit_cred_file=
      /usr/sbin/postconf: warning: /etc/postfix/main.cf: unused parameter: mydomain_fallback=localhost
      postfix/postfix-script: refreshing the Postfix mail system
      Oct 22 21:37:19 DrozBook.local postfix/postfix-script[3834]: refreshing the Postfix mail system
      Oct 22 21:37:19 DrozBook.local postfix/master[3815]: reload — version 2.11.0, configuration /etc/postfix

  • Reply Zak Fjeldheim |

    It looks like I’m receiving two errors.

    Oct 28 13:51:46 Zaks-Accreon-MacBook-Pro.local postfix/smtp[3679]: 24AAB2B91B1: SASL authentication failed; cannot authenticate to server smtp.gmail.com[74.125.22.108]: generic failure
    Oct 28 13:51:46 Zaks-Accreon-MacBook-Pro.local postfix/smtp[3680]: connect to smtp.gmail.com[2607:f8b0:400d:c04::6d]:587: No route to host

    One saying I can’t authenticate and the other saying “No route to host.” I checked my username and password and they are correct.

    Thoughts?

  • Reply Michael Bühlmann |

    I configured /etc/postfix/main.cf
    I get the error message:
    /usr/sbin/postconf: warning: /etc/postfix/main.cf: unused parameter: mydomain_fallback=localhost

    I work with OS X Yosemite.

    What do I have to change?

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